We've recently transitioned Eliza into her new and hopefully long time use bed. Last summer, I remember switching her out of the crib to a toddler bed at around 15.5 months, in preparation of Nolan coming later on. Plus, I didn't want her to find out that she was capable of being able to climb out of the crib.
As you can see, when Mr. G came home one night and checked in on her first nights sleep, this is how we found her. she fell out and into her treasure chest of stuffed animals and could have cared less.
The next night, a guardrail went in that came with the separated hand me down bunk beds upper bunk. All in all, the transition has gone pretty smooth with no real tears when I took the bed out to the garage for when Nolan is ready for that milestone. There were also no tears for mommy either. We will continue using most of the toddler bedding with the exception of the fitted sheet until she can make her own bed :)